Hoarding, rationing, and the next dollar problem

I have recently found myself in what should be an enviable position for any travel hacker: I’ve booked all my upcoming flights and stays, used up my quarterly and semi-annual credits, and am still sitting on all the miles and points I could conceivably use through the rest of the year.

Of course, instead of giving me a chance to relax and take a break, this objectively great situation has me thinking more about how to approach travel hacking, and everything-else hacking, on the scale of years instead of months.

Hoarding

I think of myself as the kind of person who tries to strictly manage their loyalty balances, not out of moral superiority, but for the simple reason that by definition I’m virtually always earning loyalty currencies based on their current value (with the interesting exception of anticipated mergers and transfer opportunities, like the Hawaiian-Alaska merger).

The longer I let balances sit, the less likely I am to redeem them at that current value. In other words, I know the value of my points at their current redemption values, and earn them on that basis, but the longer they sit in my accounts, the less likely their ultimate redemption value will be the same.

It’s vital to differentiate between two meanings of “devaluation,” since they’re often used interchangeably. The top Hyatt redemption tier, to give a simple example, used to be at 30,000 Hyatt Gold Passport points for the seven top-tier Park Hyatt properties in the system. I used to even be able to name them all off the top of my head, although I only ever stayed in Zurich and Vienna, where you get to swim in the old Bank of Austria’s vault and eat breakfast in the old cashier’s hall — a good time!

World of Hyatt’s Category 8 now goes up to 45,000 points, with the Park Hyatts (Parks Hyatt?) in Tokyo, Paris-Vendome, Zurich, and the Maldives Hadahaa joining that category, while the other formerly “top” properties (Vienna, Sydney, and Tokyo) are still in Category 7, which now costs up to 35,000 points thanks to the introduction of seasonal pricing.

These are devaluations, if you mean that holding everything else equal, the same hotel costs more points per night. But of course, all else isn’t equal.

At the level of an individual hotel, properties age and get worn out, and get renovated and refreshed. Where the property is in that cycle should matter when deciding whether points have “really” lost value: you may have fond memories of paying 3,500 points for the rundown Category 1 where you spent your honeymoon and be disappointed it’s now Category 4. But if it’s moved up in categories because they did a gut renovation, then you may find it’s an even more romantic getaway on your 10th anniversary.

At the global level, it doesn’t matter if individual properties move up or down in categories; it only matters how much of your home currency’s value you get across all the redemptions you actually make. In the golden age of blogs and forums people often argued that using cash prices gave inflated values because we would not be able to take the trips we do without travel hacking, so it’s unreasonable to claim points “saved” you the amount of money a trip would cost that you never would have taken.

This supposed problem is just a rhetorical trick though, since people who are not travel hackers, including former and future travel hackers, still take vacations. The correct value to use in calculating your savings is neither the cash price of the hotels you stay in or the flights you take, it’s the money you would otherwise spend on the vacations you would actually take.

Rationing

I call it “hoarding” points when people accumulate more than they can realistically anticipate using in the near-term, running the risk of devaluation. Rationing is the counterpart of hoarding on the redemption side: someone is unwilling to use points except above some minimum value, and for lower-value redemptions uses cash instead.

The problem with rationing is not that it’s bad to get as much value as possible from your loyalty currencies. The problem is that if you’re regularly spending cash instead of miles and points for your travel, you’re probably not earning enough cash, and the same time and money you spend earning loyalty currencies would be better spent on earning cash and cash equivalents.

For example, both the US Bank Flexperks Travel Rewards and American Express Hilton Surpass cards earn bonus points at grocery stores: Flexperks earns 2 Flexpoints per dollar and Surpass earns 6 Hilton Honors points per dollar.

Flexpoints are worth 1.5 cents each when redeemed through the US Bank travel portal, so the Flexperks card earns the equivalent of 3% in cash.

If you spent $10,000 on each card, you’d have $300 worth of travel value or 60,000 Hilton Honors points. There are many cases where 60,000 points can get you more than $300 worth in stay value, especially when using Hilton’s 5th night free benefit, so say you decide to use the Surpass for that spend.

On your next trip, you see a 60,000-point Hilton is available, but you find a cash rate for $250 after taxes and fees, or just 0.4 cents per Hilton point. Since you’re afraid of having “wasted” that $10,000 in spend, you ration your Hilton points and pay cash for the stay instead.

The problem in this case is obvious: you’ve now spent however much it cost to manufacture $10,000 in spend, and you’ve spend $250 on a hotel stay.

If this happens once, there’s no harm done: you can still use the Hilton points on a future stay. But if you find this happening over and over again, then you are probably valuing Hilton points too highly; they probably are not actually worth 0.5 cents to you, and you should be using a different, lower value for them when deciding whether to earn or redeem cash or a different currency instead.

The next dollar problem

On the redemption side this is a version of the “sunk cost” fallacy: it doesn’t matter what you paid for your points, the only thing that matters is whether you will save money by redeeming them now or holding on to them for later.

When it comes to personal finance, I call this the “next dollar” problem, which is closely related to my concept of compounding discipline: what do you do with the next dollar you earn?

Personal finance columns often set out to make these choices sound easy: should you use the next dollar you earn to pay off low-interest student loan debt or high-interest credit card debt? Should you invest in a taxable account before maxing out your retirement contributions?

Sometimes this is explicitly framed in terms of the next dollar, for example the advice to “save every raise” by increasing your 401(k) contribution rate each time your salary increases, so your take-home pay stays the same.

It’s not important to me in the slightest what you decide to do with your next dollar. The point of this exercise is to think about it in advance. For example, should you pay off credit card debt before you make IRA contributions? There are anti-debt and economic literalists who tell you the answer has to be yes: you should rank all your debt by interest rate, start and the top, and every dollar goes into paying off those balances one-by-one before you start saving money.

There are obviously people for whom and times when that’s the right decision, but it’s equally true to describe this as a decision between putting the next dollar into an account protected in bankruptcy or paying of a balance dischargeable in bankruptcy. The more likely you are to find yourself in bankruptcy court, the less inclined you should be to do your creditors any favors.

As for me, I’m currently putting my “next dollars” into Prosper peer-to-peer loans and towards filling up my fourth rewards checking account (if you’re wondering, I have two next dollars because investing with Prosper is an extremely slow process unless you’re willing to lower your risk threshold or increase your per-loan investment, neither of which I’m willing to do).

In a month or two I’ll have met my goals for both those accounts, but there will still be a next dollar. I still have a balance on my Small Business Administration loan from the pandemic with a 3.75% adminstered interest rate, which I could accelerate payments towards, although that’s a lower return than I’m used to getting from my next dollar; even cash in my brokerage accounts earns more. I’m far from the maximum annual contribution to my solo 401(k), so I could move my weekly contribution up, which has the advantage of providing automatic compounding discipline within the account itself.

Like I say, I’ve got a couple months to think about it, but thinking about it I will be.

Two steps forward and one step sideways with Hyatt awards

I’ve seen a number of people write about two big improvements to the World of Hyatt award booking system: during the reservation process, Guest of Honor Awards (giving the guest Globalist privileges during their stay) and Suite Upgrade Awards can now be selected and applied online while make an all-cash or all-points reservation.

Previously, these awards could only be applied over the phone after a reservation had been made. Unfortunately, these awards still cannot be combined with each other or with Pay Your Way reservations, either online or over the phone. Let’s discuss.

“Pay Your Way” lets you use points, cash, and free night awards on a single reservation

I use this feature all the time, but it doesn’t offer any special value except convenience: most chains require you to “check out” and “check back in” when you move between different payment types and reservation channels, but as long as you’re booking through Hyatt you can combine points, cash, and free night awards however you like, as long as the same rate and room type is available for each night, saving you (or, God forbid, a loved one) a trip or two to the front desk during your stay to remake your keys.

That lets you use cash for the nights that are cheapest with cash, points for the nights that are cheapest with points, and free night awards for the most expensive nights (since Hyatt free night awards are classified by property category, not specific point values).

Again, this does not save you any money, points, or awards, as long as each of the nights is available on its own, although it may help you meet a minimum stay requirement during especially busy times if a property won’t let you book the nights individually.

Suite Upgrade Awards and Guest of Honor awards can be used online but can’t be combined with free night awards (or each other)

What many people have been talking about is the ability to apply Suite Upgrade Awards and Guest of Honor awards online at the time of booking. This is fine and good, but it’s only half the story.

As a reminder, Suite Upgrade Awards allow you to confirm an upgrade to a property’s entry-level suite, if available at time of booking. Previously, these awards had to be redeemed by calling into Hyatt. Now, there’s a radio button to click that lets you see if there’s an available suite and redeem the award for it during the booking process.

Guest of Honor awards give the guest (including yourself, if applicable), World of Hyatt Globalist status benefits during a stay, the most important of which are generally considered to be free breakfast, free valet parking (on award stays), waived resort fees, late checkout, and suite upgrades, if available at check-in.

So while it’s obviously not especially common, you can imagine a situation where you might want to apply a Suite Upgrade Award to a Guest of Honor booking, since the benefits are very slightly different. You want your in-laws to have free breakfast and late check-out but you also want to make sure they get a suite for their gazillionth anniversary instead of counting on hope or an e-mail to the general manager.

That’s not possible, since only one award can be applied to a reservation.

The problem and the easiest workarounds

That’s an extreme case, but a much more obvious situation is a Globalist or friend-of-a-Globalist trying to apply a Suite Upgrade Award to a Pay Your Way reservation, which happens to be the precise situation I found myself in the other week. I’d identified an upcoming Category 7 Andaz stay as a perfect redemption storm: a Category 1-7 free night award for the most expensive night and points for the cheaper ones, all made in a single online reservation through the convenience of Pay Your Way.

But as you’ve gleaned by now, it doesn’t work. You can’t apply a Suite Upgrade Award to a Pay Your Way reservation online, but Hyatt can’t apply it over the phone either.

How much of a problem this is depends on which nights you intended to apply the free night award to. Hyatt is better, in my experience, at detecting and combining reservations in advance, so if you’re using the free night award for your last night, you can just use the Suite Upgrade Award for the first nights of the reservation (booked with cash or points) and you’ll have a chance verging on 100% of simply being left in the same suite for the last, “ineligible” night.

This is less likely to work if the night you want to use the free night award on falls in the middle of your stay, but I suspect the odds are still pretty good.

I hesitate to venture a guess on how the billing would work out if you tried this with a Guest of Honor award, since many of those benefits are literally billed daily or nightly: breakfast, valet parking, resort fees.

Conclusion

World of Hyatt has been in a class by themselves when it comes to resisting the devaluation of their points and free night awards, and I am going to rely on them more in 2025 since I qualified for Globalist in 2024 for the first time since taking advantage of the Starwood-Marriott status match years ago.

But I’m not here to give them any more credit than they deserve: the system is still pretty annoying and I hope this post makes it slightly less annoying for the next guy.

Don't forget resort fees when pricing Guest of Honor awards on paid stays

World of Hyatt elite “milestones” are, in addition to being a clever marketing gimmick, one source of additional value you accumulate as you earn elite qualifying nights each year. I recently broke down their value methodically here and shared my experience with “2K Next Stay Awards.”

At 40, 60, 70, 80, 90 elite-qualifying nights, and every 10 nights after 110 elite-qualifying nights, you automatically earn Guest of Honor Awards in addition to an award you choose. These awards allow you to give anyone (including yourself) the “in-hotel” benefits of being a Globalist elite. In addition to the breakfast and lounge access benefits most people are familiar with, and the guaranteed 4:00 pm checkout that’s my own favorite benefit, Globalists and Guests of Honor also get resort fees waived on paid stays.

The tricky part is that Hyatt does not remove resort fees from their pricing summary when you apply Guest of Honor awards online, which, if you’re not aware of it, will cause you to misvalue your World of Hyatt points.

You can see this clearly in these two screenshots, where a resort fee appears at checkout whether or not a Guest of Honor award is attached to the reservation:

Most of the time this doesn’t make a decisive difference: World of Hyatt points are usually so valuable that whether they’re “slightly more” or “slightly less” valuable doesn’t impact your booking decision.

Once you’re aware of the issue, however, it’s easy to imagine corner cases like the one I stumbled into at The Lodge At Spruce Peak, where I found the rates shown above. A Category 8 property, the hotel starts at 35,000 points per night during “off-peak” periods, and costs between 40,000 and 45,000 points per night during ski season.

At $424.08 per night off-peak, that’s already a marginal points redemption at 1.21 cents per point; you could book it through the Chase travel portal for fewer Ultimate Rewards points than transferring them to Hyatt.

But at the true price of $376.38 (after subtracting the waived resort fee and tax), it’s a truly godawful redemption at just 1.08 cents per point.

Conclusion

In the grand scheme of things, properties that charge resort fees are likely on the more expensive end of Hyatt’s portfolio, and thus likely to be solid enough point redemptions that a waived resort fee won’t change your booking calculus. But at highly seasonal properties, cash rates may drop by much more than points rates, while resort fees stay flat and make up a larger share of the total cost in cash.

In those circumstances, applying a Guest of Honor award to a paid rate may turn a marginal redemption into an outright bad one.

Can Hyatt promo codes override seasonal cancellation policies?

Over the New Year holiday I braved the madness that is flying Southwest Airlines and took a weeklong trip down to Playa Del Carmen, Mexico. While putting the trip together, I noticed something curious as I sifted through the hundreds of hotels lining Quintana Roo’s coast: using a Hyatt promo code seemed to remove the restrictive cancellation policy at the hotel I ultimately chose. Since I didn’t need to cancel the stay, I’m not certain this is replicable or even useful, but I wanted to put the possibility on readers’ radars.

Planning my stay

Sparing the details of how I narrowed down the options, I finally settled on the Thompson Playa Del Carmen Main House, which had a nice combination of being both “in town” as opposed to the isolated beachfront resort hotels and a Hyatt property which at 15,000 points per night was an order of magnitude cheaper than any other hotel I was seriously considering.

The plan was complicated, in a good way, by the fact that I had two stackable American Express Offers, one for $60 off $300 spent at any Thompson in the world, and the second for $100 off $400 spent at any Hyatt property in Latin America. I also had over $1,000 in Hotels.com gift cards I got from Cardcash in an earlier gift card exchange.

This meant I wanted to break my weeklong stay into three pieces: paying for the most expensive nights with Hyatt points and a free night award certificate, paying for the cheapest night with my American Express card in order to trigger $160 off $400 (I used room charges to “top up” my bill to $400, since the cheapest of the 7 nights was only $379.90 after tax), and paying for the remaining nights using my Hotels.com gift card.

Cancellation policies, promo codes, and “Pay Your Way”

Since I was looking for the cheapest night to pay with my American Express card, I started on my irregularly-updated Hotel Promotions page and saw that the promo code “GOJALIN15” was offering up to 15% off paid stays. When I plugged that code into Hyatt’s “Special Offer Code” field, the rate popped right up.

This Thompson property, at least between Christmas and Epiphany (apparently a big deal in Quintana Roo), had a 30-day cancellation policy on award reservations and on all the normal paid rates I found. Inside of that 30-day window, no changes or cancellations were permitted without forfeiting the entire price of the stay.

The GOJALIN15 rate did not have that restriction. Instead, it had the standard 3-day cancellation policy you’ll find on stays if you go searching right now. This wasn’t particularly interesting on its own: I only wanted to book one night with cash, and the 30-day cancellation rate was much cheaper than the GOJALIN15 rate.

What got my attention was that when I clicked through the GOJALIN15 rate, I was offered the ability to “PAY MY WAY,” Hyatt’s booking feature that allows you to combine paid nights and award nights on a single stay. And using that option, the favorable cancellation policy passed through to the PAY MY WAY booking page.

Two observations follow from this, one actionable, the other merely interesting. The interesting point is that some (or all!) coupon codes generate PAY MY WAY-eligible rates; typically only "standard” and “member” rates are eligible for PAY MY WAY, so it’s nice to be able to identify potential future exceptions.

The more practical consideration is that if you plan to redeem points for a stay with unfavorable cancellation conditions, but can use a coupon code that applies more generous terms to the whole stay, then you might be able to “buy” a more flexible cancellation policy by paying for one night of the stay with cash.

Additional considerations

That’s the potential play, as far as it goes, but there are two more wrinkles.

First, it seems that even if you use PAY MY WAY on a coupon code with favorable cancellation terms, if you pay entirely with points or award certificates, then the stay is treated entirely as an award stay and the cancellation terms revert to the standard ones after making the reservation. In other words, you can’t change the cancellation policy on an award reservation merely by clicking the PAY MY WAY button.

I say “after” making the reservation because all through the booking process the more generous coupon code terms were shown. It was only after making my reservation and receiving the confirmation e-mail that I saw the 30-day cancellation policy on my reservation. I think this gives you a pretty airtight case for having the more favorable terms manually applied, as long as you are sure to take plenty of screenshots during the booking process.

Second, because I didn’t ultimately make a “mixed” PAY MY WAY reservation, I don’t know if the same thing would have happened in that case. If so, I still think the case for invoking the “original” more generous terms would be ironclad, but it’s never ideal to get into a position where the score is up to the ref.

Conclusion

I’m aware that what I’m describing is a fairly advanced corner case. You need to have a working coupon code that is set up with favorable cancellation terms (GOJALIN15 expires February 28, 2024), a property with unfavorable cancellation terms during your stay, and a stay with at least one paid night cheap enough to justify paying in cash to swap the cancellation policies — plus the willingness to fight for your points back if you do need to cancel the reservation in the window between the favorable and unfavorable policies.

And if you don’t ultimately cancel the reservation, then you’ll never know whether it “worked” or not!

Comparing IHG's 4th-night-free with Marriott and Hilton's 5th-night-free

I was reading Danny the Deal Guru’s write-up of the latest Chase IHG Rewards signup offers and something jumped out at me: the 4th-night-free benefit offered to cardholders, including those who hold the no-annual-fee IHG Rewards Traveler card. To be clear, this isn’t a new benefit, it’s just one I haven’t had a chance to think about in depth.

Generally speaking, I don’t rate IHG or their rewards program very highly, because while they have an enormous global footprint, they’re rarely competitive compared with the main hotel programs I rely on, Hilton and Hyatt. For example, I regularly visit Portland, OR, which on a sample search turned up two downtown Hyatt properties priced at 12,000 World of Hyatt points, a Hilton priced at 37,000 Hilton Honors points, a Marriott priced at 30,000 Bonvoy points, and a Kimpton priced at 25,000 IHG Rewards Club points (plus a nightly “amenity fee”). For a one-night stay, it would be ridiculous to choose the IHG property unless you’d built up a large orphaned balance through various shenanigans.

Since my framework is manufactured spend, not signup bonuses, it’s easy to make a direct comparison between the options:

  • 12,000 World of Hyatt points transferred from Chase Ultimate Rewards is worth $120 in cash.

  • 37,000 Hilton Honors points earned at 6 points per dollar with the American Express Surpass co-branded card is between $123 (if the same $6,200 in spend had been put on a 2% cashback card) and $185 if the points were purchased for 0.5 cents each, an offer which is regularly available, including now through March 7, 2023.

  • 30,000 Marriott Bonvoy points are worth between $240 (if you bought the points during one of their periodic promotions) and $300 (if you transferred the points from Chase Ultimate Rewards.

  • 25,000 IHG Rewards points are worth between $150 and $175 if you buy them using the “points and cash” trick (purchasing points while making an award reservation, then cancelling the reservation and having the points refunded to your account).

This makes comparing the four sample reservation options, and indeed comparing all reservation options at the four chains, easy, if on average:

  • World of Hyatt points cost 1 cent each;

  • Hilton Honors points cost 0.42 cents each;

  • Marriott Bonvoy points cost 0.9 cents each;

  • and IHG Rewards points cost 0.65 cents each;

then on a one-night stay you can convert the points cost of any property into the cash cost of manufacturing, transferring, or purchasing the required points. In the concrete example above, we saw that Hyatt and Hilton were quite competitive, while Marriott and IHG Rewards were significantly more expensive options.

On four-night stays, the equation changes, but only for IHG Rewards points. On four-night stays at the other three chains, the cost per point remains the same, while the 4th-night-free benefit offered by the IHG Rewards credit cards increases their value by 33% or decreases their cost by 25% to 0.49 cents each — same difference. The four-night IHG Rewards stay now costs just $122 per night, putting it squarely in the middle of the “competitive” pack of Hyatt and Hilton, or even on the cheaper end (ignoring that pesky Kimpton amenity fee, which you obviously shouldn’t in practice).

Moving to a five-night stay, the equation shifts again, but this time against IHG Rewards, since Hilton and Marriott both offer the fifth night free on award stays. The cost per night on the sample five-night stays with Hilton is $123 per night, with Marriott is $216, and with IHG $130. Hyatt doesn’t offer free nights on longer stays so their cost per night remains flat at $120.

Reference Card

I wanted to use a specific example to explain why I personally don’t care for IHG Rewards, but in case you want to bookmark this post or paste the values into your notes app, here are the shortcuts when calculating the cost of stays of various lengths.

Stays of 1-3 nights:

  • World of Hyatt: 1 cent per point

  • Hilton Honors: 0.42 cents per point

  • Marriott Bonvoy: 0.9 cents per point

  • IHG Rewards: 0.65 cents per point

Stays of exactly 4 nights:

  • IHG Rewards: 0.49 cents per point

Stays of exactly 5 nights:

  • World of Haytt: 1 cent per point

  • IHG Rewards: 0.52 cents per point

  • Hilton Honors: 0.34 cents per point

  • Marriott Rewards: 0.72 cents per point

Now you can easily calculate the cost of reward stays of up to 5 nights in length in every city in the world — not just in Portland, Oregon!

Combining Ultimate Rewards points, transferring Hyatt points, and Hyatt booking follies

Today’s post is a bit of an information dump, but it combines a number of issues I’ve been working through to get my trips booked for this spring and summer and that I haven’t seen covered clearly anywhere else online.

Combining Chase Ultimate Rewards points

For those of us with multiple Ultimate Rewards-earning credit cards, combining points between our own accounts is routine: earn 5 points per dollar in a quarterly bonus category, like this quarter’s grocery store bonus category on the Chase Freedom, then transfer those points to a card that allows for transfer to Chase’s travel partners or higher-value Ultimate Rewards travel portal redemptions.

But what about combining points between new household members or employees? It’s possible, but there are a few important things you need to know.

First, combining points is always done from the “sender’s” side. There’s no way to “request” points, or “pool” points held in multiple card accounts. Each sender Ultimate Rewards account has to initiate a non-reversible transfer to a “receiver” account.

Second, adding a new receiver account can no longer be done online; you’ll need to call the number on the back of your Ultimate Rewards-earning credit card and provide the recipient’s credit card number. Since my flexible Ultimate Rewards card is a business card, in my case I chose to have my sender add one of my non-flexible Freedom cards as the receiver card. I was then able to instantly convert those non-flexible points into flexible Ultimate Rewards in my legacy Ink Plus account.

Finally, senders are only allowed to add “one member of your household or owner of the company, as applicable” as recipients.

There’s a lot to unpack here. Most importantly, it means that you should not set up you and your partner as mutual recipients, since this would use up the recipient slots of each household member. Instead, it would be ideal to keep the receiver’s recipient slot open to add an additional recipient. In this way, points could be moved and consolidated in larger and larger numbers across multiple Ultimate Rewards accounts before being transferred to a single travel partner account.

Additionally, it suggests the possible value of keeping your flexible Ultimate Rewards accounts attached to separate Chase online accounts. The logic here is that while you want to preserve the flexibility of your own Ultimate Rewards points, you also may want to have more than one household transfer target, so if you have, for example, a Chase Sapphire Preferred or Reserve and a flexible Chase Ink product, you could attach separate recipient targets to each online account.

I have not experimented with this extensively, but wanted to alert readers to some interesting possibilities they can explore further for themselves.

Chase World of Hyatt point transfers are no longer instant

Transfers from Ultimate Rewards to World of Hyatt used to be immediate: log out and log back in and your balance was already updated. Regrettably, no more. I submitted a transfer on the evening of Thursday, February 17, and my points didn’t land in my World of Hyatt account until the morning of Saturday, February 19. It wasn’t the end of the world, but since I wasn’t aware of the new delay, it certainly kept me awake for a couple nights frantically refreshing my Hyatt account.

On the one hand, if you’re planning a trip weeks or months in advance, you have nothing to worry about; your points will probably arrive in plenty of time. On the other hand, if you’re frantically booking a last minute stay, don’t count on immediate Chase transfers for your Hyatt redemptions.

Member-to-member Hyatt points transfer timing

World of Hyatt, like Hilton Honors, allows members to transfer points between each other for free using the Point combining request form. For an upcoming stay, I submitted the form on Saturday, February 19. I received an immediate automated response, and the transfer was finally completed on the following Friday, February 25.

So if you’re planning to combine points in order to book an award, give yourself plenty of time to allow the transfer to go through.

Hyatt award booking chaos

Of course, combining Ultimate Rewards points, transferring them to World of Hyatt, then combining them in another member’s account aren’t done for fun. They’re done to book Hyatt awards, and this is where I ran into the truly stupefying and genuinely serious consequences of Hyatt’s new award charts and booking system.

It’s worth reminding readers of two facts:

  1. World of Hyatt properties are still defined by category;

  2. Within each category, award nights are charged at either an “off-peak,” “standard,” or “peak” rate.

This has the key corollary that a Category 1-4 free night certificate is worth 50% more on a Category 4 “peak” day than on a Category 4 “off-peak” day, saving 18,000 points instead of 12,000 points.

Now let’s get to the chaos. When booking a multi-night stay, World of Hyatt will only show you the rate available on the first night of the stay, even if the property moves from “standard” to “peak” during the stay.

To find out the nightly award rate, you have to view the property’s “Points Calendar.” Here’s the calendar for the Hyatt Place New York City / Times Square:

In this case, trying to search for a 2-night award stay will show that standard nights are available “from” 17,000 points per night.

But unless you have enough points in your World of Hyatt account to book the reservation, it will not show you the final price of 37,000 World of Hyatt points, which might lead you to transfer 34,000 Ultimate Rewards points instead, and then find out to your horror you’d run out of time to book the award.

Finally, and most egregiously, in order for award availability to appear online, the exact same room type has to be available for every night of your stay.

Putting it all together

You’ve made it this far so I don’t want to make you do any more homework and I’ll put the pieces together for you. When planning a Hyatt award and transferring Ultimate Rewards points, take the following steps in this order:

  1. Find the property you want to stay at and click the “Points Calendar” button

This will allow you to see the award rate for every night of your planned stay. Add those rates together and you will get the total cost of your stay.

2. Check standard award availability for your entire stay. Plug your hotel and dates into Hyatt and it will show you whether there is standard award availability in a single room type for your entire stay (although it will miscalculate the total cost of your stay if award rates vary by night). If so: congratulations! Transfer the required number of Ultimate Rewards points you calculated in Step 1 to Hyatt and hope the space is still available when the transfer is completed.

3. If standard award availability isn’t available for your entire stay, don’t despair. It may be the available room types simply shift during your stay. Now comes the boring part: check each day of your stay individually for standard award availability, and book “clusters” of nights in each room type. For example, standard award availability might be available in a two queen room for 2 nights, a one king room for 2 nights, and an accessible king room for 1 night. Book them each separately.

4. If necessary, call the hotel and ask to stay in the same room for your entire stay across all your reservations. They might not accommodate you, depending on the circumstances, but moving your crap around a single hotel is a lot easier than moving between hotels, which I’m not too proud to confess I’ve done more than once over the years.

How I think about hotel free night certificates

I gather from my RSS feed reader that American Express has launched an aggressive campaign to move more Hilton co-branded credit cards in the new year, with the highest bounties naturally being paid to those who sell the most of their ultra-premium Aspire cards. And if you’re selling Aspire cards, you naturally need to play up the value of the annual free weekend night certificate. I like free nights, I like free flights, I like free car rentals, I like free groceries: I like everything free. But that doesn’t mean everything free is created equal, and free night certificates are one of the easiest, and most expensive, traps to fall into.

A free night certificate is worth its opportunity cost…

This is the commonsense idea that you should not value any award based on the retail price of its paid equivalent, but rather the amount you yourself would actually pay under the same circumstances. This is best illustrated in cities where multiple “reasonable” booking options exist.

Take, at the high end, New York City, where the Conrad New York Midtown, a Hilton property, is located about a third of a mile from the Park Hyatt New York. On a random day in mid-June, the Conrad is charging 95,000 Honors points per night, while the Park Hyatt charges 30,000 World of Hyatt points. The equivalent flexible paid rates are $945.30 and $1,202.63, respectively.

First, let’s state the obvious: these are great redemptions! If you became a travel hacker to get a taste of luxury you could never otherwise afford, then manufacturing about $15,000 in grocery store spend on a Hilton Surpass card, or $6,000 in office supply store spend on a Chase Ink Business Cash card, for a night in the lap of luxury in the heart of the metropole is just what you’re after.

…properly understood

But that’s not a strategy, because a strategy needs to take into account your overall travel preferences and needs. Even though it’s precisely what I was looking for, I admit I was still a bit surprised when I realized that 5 nights at the “DoubleTree by Hilton New York Times Square South,” about a mile from the Conrad, is going for just 40,000 Honors points per night, or 160,000 points for 5 nights after the 5th-night-free is applied for Hilton Honors elites. A flexible paid reservation in the same period runs about $1,658 (another great Honors redemption!).

Adding a 6th night to your stay at the DoubleTree using a free weekend night certificate will only save you $332, or 40,000 additional points, a much worse value than redeeming it at the Conrad. However, the redemption allows you to avoid changing properties 1 or 5 nights into a 6-night stay. In other words, maximizing the value of your free night certificate may cost you more in wasted vacation time and family disharmony than any cash savings your mental accounting conjures up.

Free night certificates have different value as different parts of a strategy

The key to integrating free night certificates into your travel hacking strategy is to ask yourself, “where do I stay, for how long, and why?”

Over the New Year holiday, my partner and I flew to Hawaii and stayed at the Grand Naniloa Hotel Hilo, where award nights cost 50,000 Honors points. Our initial plan was to spend 7 nights there: 6 nights for the price of 5 thanks to the 5th-night-free benefit, and the seventh night using my Hilton Honors Surpass free night certificate from spending $15,000 on the card in 2021. I don’t have the cash cost in front of me, but I remember it worked out to “roughly” a 1 cent-per-point redemption.

About halfway through our stay, we decided to spend the last night closer to our departure airport, Ellison Onizuka Kona International Airport at Keahole, so I cancelled our 7th night in Hilo and made a reservation with the same certificate at the 65,000-point Hilton Waikoloa Village.

The essential thing I want to highlight is that this did not save me any money! Moving our last night from a 50,000-point property to a 65,000-point property was an absolute wash, and did not increase the value of the certificate in any way. I even got an identical $30 daily food and beverage credit at both properties.

And this is the case more often than you would imagine. Since most experienced travel hackers have lots of booking options all the time, you should not expect any one booking instrument to consistently provide outsized value. Rather, having multiple instruments available allows you to select the one that serves your needs the best in any given situation.

Are Hyatt free nights more valuable than Hilton free nights?

I’m an unapologetic defender of the Hilton Honors program and especially the American Express Surpass card. Earning 6 Honors points per dollar on grocery store manufactured spend, combined with the 5th night free on award redemptions, makes it an outstanding play for my particular travel hacking strategy.

But I’m also not an idiot: transferring Ultimate Rewards points to Hyatt is a fantastic way to get 3 or more cents per point in value from the Ultimate Rewards points I manufacture at office supply stores, and on Freedom cards during this quarter’s 5-point-per-dollar grocery store bonus category.

While World of Hyatt free night certificates can only be redeemed at category 1-4 properties, World of Hyatt also doesn’t offer the 5th-night-free benefit Hilton Honors (and Marriott Bonvoy) does, meaning I’m never “wasting” points by redeeming a Hyatt free night certificate: each free night corresponds to the exact number of points I would have had to spend on that exact night.

A Category 1-4 Hyatt free night certificate can be swapped in at any place in a trip at its exact points value, without jeopardizing the value of the overall redemption. On the other hand, a 4-night Hilton points redemption can always be extended for a fifth night, either at the beginning or end of the reservation, without incurring any additional cost.

Hilton free night certificates are therefore most valuable if you find yourself consistently making short term, expensive stays, or extending award reservations beyond 5 nights. Under those conditions, the sweetest spots will always be one-night stays and adding 6th nights to stays you’ve already redeemed points for at the most valuable properties in the system.

Conclusion: Surpass earning versus Aspire certificates

For folks with multiple players in their household, this circle is easily squared, by combining one partner’s earning ability with the Surpass and the other partner’s annual statement credits and free night certificates with the Aspire. That’s a great way to play the game. But if you’re playing solo or with a reluctant (or bored) partner, the flexibility of the Surpass’s earning ability and the value of the World of Hyatt credit card’s free night certificates far outstrip the one-off gimmicks of the ludicrously expensive Aspire.

Matching Hyatt Explorist or Globalist status to MLife Gold status in 9 words

  1. Click here

  2. Log in

  3. Click “OPT IN”

  4. Log in

Your MLife status will be matched in 10-15 minutes, in my experience, although you do need to log out and log back into MLife to see your updated status.

I’m offering these 9 words as a public service, because I don’t do any “search engine optimization” or care about the amount of traffic my site gets, and every other blog I’ve seen write about this status match takes up to 560, 713, or in one particularly extreme case, 1,088 words without describing the actual actions required to match status.